I’m a 30-year-old woman who lives with my gay best friend. Our friends affectionately call us Will and Grace. We both hold down decent jobs, spend lots of time exploring the city, and we’ve set up an ideal household: delicious meals, my adorable dog whom we both love, wonderful dinner parties and movie nights. But we both find it hard to get dates with relationship-available men. We do online dating, encourage each other and set each other up when possible. When we’re out, we act as wing-man and -woman. Still, our love lives are not as thriving as we’d like, and I wonder if somehow us living together and having a “happy household” is impeding us from finding that with the “real” families we both want.
He Said: Congratulations on refusing to fall into the gay guy/straight girl trap of using each other as non-sexual lovers to avoid the challenges of real sexual and emotional intimacy. However, you should start on your dating adventures by appreciating what you have—and stop longing for a romantic ideal of a family that may never happen and will certainly never happen the way you fantasize it will. Whether you two live together as best friends for one more year or ten, try to enjoy every second by living for the present rather than an imagined future. Ironically, it will make you both more dateable and less desperate.
On a more practical level, dating is basically a numbers game. You need 99 toads to find one prince. So I propose, as they say in SF, gamifying your dating lives. Challenge each other to find at least one date per week with the reward being having the house to yourself on the night of. Source your men everywhere: On hookup sites, dating sites, even Facebook. Approach guys in bars on behalf of each other. Ask friends to put out the word that you are looking. Make this a conscious, proactive search, as you would a job hunt. But run this campaign with as much joy and enthusiasm as you can muster, refusing to be demoralized by rejection. You will become a fearless force not only romantically but in every facet of your life. In fact, recognize that every rejection is a step in the right direction because it means you have tried. Whatever the result, you will be better for the effort.
She Said: My gut instinct is to do just the opposite. Stop looking for a “relationship available” man. Both of you just stop it completely, for let’s say six months, as an experiment.
In six months you’ll still be 30, or 31 at most. I wish I could impart to you how very young 31 is. From my middle-aged vista it’s almost as young as 18. You have 10 good years of fertility left, more if you employ technology. Your sexual peak is a decade away. You have a good job, great friends, and an ideal household setup in one of the best cities on earth. It’s amazing how much we strive to find the one person from whom we think we will derive “everything”: best friendship, passionate sex, children, harmonious co-parenting, financial security, shared social life, functional household keeping, and oh we want fun too! Lots of fun. Till death do us part, thank you. It’s a nice dream, so nice that we go crazy trying to make it happen, and then when we do we go crazy trying to keep it happening, and then if enough of the puzzle pieces fail to materialize or fall away with time we go crazy leaving it all behind. I am asking you to simply sit still and enjoy what you have for six short months and see what happens when you stop seeking and grasping. You can go back to Match.com and the 99-to-1 rule come mid-April if need be.
And just in case this advice is too philosophical for you, here’s a more pragmatic tidbit. Just as two north poles of a magnet will repel each other, two relationship-seeking people will often repel each other, despite their best conscious intentions. It really helps the attraction principle when at least of the parties is not in seeking mode.
